DE50306588D1 - Heteroarencarboxamide zur verwendung als dopamin-d3 liganden zur behandlung von zns-erkrankungen - Google Patents
Heteroarencarboxamide zur verwendung als dopamin-d3 liganden zur behandlung von zns-erkrankungenInfo
- Publication number
- DE50306588D1 DE50306588D1 DE50306588T DE50306588T DE50306588D1 DE 50306588 D1 DE50306588 D1 DE 50306588D1 DE 50306588 T DE50306588 T DE 50306588T DE 50306588 T DE50306588 T DE 50306588T DE 50306588 D1 DE50306588 D1 DE 50306588D1
- Authority
- DE
- Germany
- Prior art keywords
- treatment
- disorders
- cns diseases
- heteroare
- dopamin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract 3
- 150000003857 carboxamides Chemical class 0.000 title 1
- 201000010099 disease Diseases 0.000 title 1
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title 1
- 229960003638 dopamine Drugs 0.000 title 1
- 239000003446 ligand Substances 0.000 title 1
- -1 4-phenyl-1-piperazinyl Chemical group 0.000 abstract 3
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 abstract 2
- 208000035475 disorder Diseases 0.000 abstract 2
- 230000033001 locomotion Effects 0.000 abstract 2
- 101710155073 2-amino-3,7-dideoxy-D-threo-hept-6-ulosonate synthase Proteins 0.000 abstract 1
- 206010001540 Akathisia Diseases 0.000 abstract 1
- 208000007848 Alcoholism Diseases 0.000 abstract 1
- 206010008531 Chills Diseases 0.000 abstract 1
- 208000022497 Cocaine-Related disease Diseases 0.000 abstract 1
- 208000012661 Dyskinesia Diseases 0.000 abstract 1
- 208000014094 Dystonic disease Diseases 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 208000010412 Glaucoma Diseases 0.000 abstract 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 abstract 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 abstract 1
- 206010057852 Nicotine dependence Diseases 0.000 abstract 1
- 208000026251 Opioid-Related disease Diseases 0.000 abstract 1
- 208000018737 Parkinson disease Diseases 0.000 abstract 1
- 208000001431 Psychomotor Agitation Diseases 0.000 abstract 1
- 208000005793 Restless legs syndrome Diseases 0.000 abstract 1
- 201000001880 Sexual dysfunction Diseases 0.000 abstract 1
- 208000025569 Tobacco Use disease Diseases 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 208000015114 central nervous system disease Diseases 0.000 abstract 1
- 229960003920 cocaine Drugs 0.000 abstract 1
- 201000006145 cocaine dependence Diseases 0.000 abstract 1
- 208000010877 cognitive disease Diseases 0.000 abstract 1
- 206010013663 drug dependence Diseases 0.000 abstract 1
- 208000010118 dystonia Diseases 0.000 abstract 1
- 208000013403 hyperactivity Diseases 0.000 abstract 1
- 208000031424 hyperprolactinemia Diseases 0.000 abstract 1
- 208000015122 neurodegenerative disease Diseases 0.000 abstract 1
- 239000003176 neuroleptic agent Substances 0.000 abstract 1
- 230000000701 neuroleptic effect Effects 0.000 abstract 1
- 229940127240 opiate Drugs 0.000 abstract 1
- 201000005040 opiate dependence Diseases 0.000 abstract 1
- 201000000980 schizophrenia Diseases 0.000 abstract 1
- 210000002265 sensory receptor cell Anatomy 0.000 abstract 1
- 231100000872 sexual dysfunction Toxicity 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 208000011580 syndromic disease Diseases 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
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- A61P27/06—Antiglaucoma agents or miotics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Psychology (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Physical Education & Sports Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE50306588T DE50306588D1 (de) | 2002-07-04 | 2003-07-02 | Heteroarencarboxamide zur verwendung als dopamin-d3 liganden zur behandlung von zns-erkrankungen |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10230062 | 2002-07-04 | ||
| DE10232020A DE10232020A1 (de) | 2002-07-04 | 2002-07-10 | Neurorezeptoraktive Heteroarencarboxamide |
| PCT/EP2003/007060 WO2004004729A1 (fr) | 2002-07-04 | 2003-07-02 | Heteroarene-carboxamides utilises comme ligands de la dopamine d3 pour traiter des maladies du snc |
| DE50306588T DE50306588D1 (de) | 2002-07-04 | 2003-07-02 | Heteroarencarboxamide zur verwendung als dopamin-d3 liganden zur behandlung von zns-erkrankungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE50306588D1 true DE50306588D1 (de) | 2007-04-05 |
Family
ID=30116602
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50306588T Expired - Fee Related DE50306588D1 (de) | 2002-07-04 | 2003-07-02 | Heteroarencarboxamide zur verwendung als dopamin-d3 liganden zur behandlung von zns-erkrankungen |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20050197343A1 (fr) |
| EP (1) | EP1519726B1 (fr) |
| JP (1) | JP2005538974A (fr) |
| KR (1) | KR20050075281A (fr) |
| CN (1) | CN1665503A (fr) |
| AT (1) | ATE354367T1 (fr) |
| AU (1) | AU2003246356A1 (fr) |
| CA (1) | CA2489396A1 (fr) |
| DE (1) | DE50306588D1 (fr) |
| DK (1) | DK1519726T3 (fr) |
| ES (1) | ES2280799T3 (fr) |
| HK (1) | HK1074579A1 (fr) |
| IL (1) | IL165677A0 (fr) |
| MX (1) | MXPA05000033A (fr) |
| NO (1) | NO20050386L (fr) |
| PL (1) | PL374612A1 (fr) |
| RU (1) | RU2320656C2 (fr) |
| WO (1) | WO2004004729A1 (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE521512C2 (sv) * | 2001-06-25 | 2003-11-11 | Niconovum Ab | Anordning för administrering av en substans till främre delen av en individs munhåla |
| ES2285233T3 (es) | 2002-12-20 | 2007-11-16 | Niconovum Ab | Un material en particulas que contiene nicotina y celulosa microcristalina fisicamente y quimicamente estable. |
| DE102004037445A1 (de) * | 2004-08-02 | 2006-03-16 | Schwarz Pharma Ag | Carboxamide des Indolizins und seiner Aza- und Diazaderivate |
| DE102004054634A1 (de) * | 2004-11-12 | 2006-05-18 | Schwarz Pharma Ag | Azaindolcarboxamide |
| DE102004063797A1 (de) * | 2004-12-30 | 2006-07-13 | Schwarz Pharma Ag | Sauerstoffhaltige annelierte Phenylpiperazin- und Phenyldiazepancarboxamide |
| NZ555491A (en) * | 2005-01-03 | 2010-01-29 | Univ Siena | Aryl piperazine derivatives for the treatment of neuropsychiatric disorders |
| WO2007104573A2 (fr) | 2006-03-16 | 2007-09-20 | Niconovum Ab | Composition améliorée de tabac à priser |
| FR2903986A1 (fr) * | 2006-07-21 | 2008-01-25 | Pierre Fabre Medicament Sa | Nouveaux derives chromenes ou thiochromenes carboxamides, leur procede de preparation et leurs applications en therapeutique |
| US8748608B2 (en) | 2007-06-15 | 2014-06-10 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | 4-phenylpiperazine derivatives with functionalized linkers as dopamine D3 receptor selective ligands and methods of use |
| US9227944B2 (en) | 2008-10-10 | 2016-01-05 | Institute Of Pharmacology And Toxicology Academy Of Military Science P.L.A. China | Dopamine D3 receptor ligands and preparation and medical uses of the same |
| WO2010040274A1 (fr) * | 2008-10-10 | 2010-04-15 | 中国人民解放军军事医学科学院毒物药物研究所 | Nouveaux ligands de récepteurs d3 de la dopamine, leurs procédés de préparation et leurs applications |
| FR2949465B1 (fr) * | 2009-09-01 | 2011-08-12 | Pf Medicament | Derives chromones, leur procede de preparation et leurs applications therapeutiques |
| US11299476B2 (en) | 2016-03-14 | 2022-04-12 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Dopamine D3 receptor selective antagonists/partial agonists; method of making; and use thereof |
| WO2020055725A1 (fr) | 2018-09-11 | 2020-03-19 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Antagonistes/agonistes partiels sélectifs du récepteur d3 de la dopamine et utilisations associées |
| CN114409621B (zh) * | 2022-02-09 | 2023-09-08 | 江苏省原子医学研究所 | 一种靶向多巴胺d3受体的诊疗药物及其应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3646048A (en) * | 1970-02-02 | 1972-02-29 | American Cyanamid Co | N-(tert-aminoalkyl)-2-indenecarboxamides |
| US3646047A (en) * | 1970-02-02 | 1972-02-29 | American Cyanamid Co | Certain benzo(b)thiophene-2-carboxamide derivatives |
| NL8005133A (nl) * | 1980-09-12 | 1982-04-01 | Duphar Int Res | Fenylpiperazinederivaten met antiagressieve werking. |
| US5106849A (en) * | 1988-05-24 | 1992-04-21 | American Home Products Corporation | Use of aryl- and heteroaryl piperazinyl carboxamides in the treatment of various central nervous system disorders |
| IL90279A (en) * | 1988-05-24 | 1995-03-30 | American Home Prod | History of piperazinyl carboxamide, their preparation and the pharmaceutical preparations containing them |
| ES2027898A6 (es) * | 1991-01-24 | 1992-06-16 | Espanola Prod Quimicos | Procedimiento de preparacion de nuevos derivados de la 2-metoxifenilpiperacina. |
| SE9201138D0 (sv) * | 1992-04-09 | 1992-04-09 | Astra Ab | Novel phthalimidoalkylpiperazines |
| DE4425146A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung heterocyclischer Verbindungen |
| DK0891344T3 (da) * | 1996-04-05 | 2003-04-07 | Sod Conseils Rech Applic | Antagonister til alpha-1-adrenergisk receptor |
| HUP0103987A3 (en) * | 2001-09-28 | 2004-11-29 | Richter Gedeon Vegyeszet | Phenylpiperazinylalkyl carboxylic acid amid derivatives, process for their preparation, pharmaceutical compositions containing them and their intermediates |
-
2003
- 2003-07-02 KR KR1020047021525A patent/KR20050075281A/ko not_active Application Discontinuation
- 2003-07-02 ES ES03762588T patent/ES2280799T3/es not_active Expired - Lifetime
- 2003-07-02 EP EP03762588A patent/EP1519726B1/fr not_active Expired - Lifetime
- 2003-07-02 WO PCT/EP2003/007060 patent/WO2004004729A1/fr active IP Right Grant
- 2003-07-02 DK DK03762588T patent/DK1519726T3/da active
- 2003-07-02 MX MXPA05000033A patent/MXPA05000033A/es not_active Application Discontinuation
- 2003-07-02 AU AU2003246356A patent/AU2003246356A1/en not_active Abandoned
- 2003-07-02 US US10/519,487 patent/US20050197343A1/en not_active Abandoned
- 2003-07-02 PL PL03374612A patent/PL374612A1/xx unknown
- 2003-07-02 RU RU2004139041/04A patent/RU2320656C2/ru not_active IP Right Cessation
- 2003-07-02 AT AT03762588T patent/ATE354367T1/de not_active IP Right Cessation
- 2003-07-02 DE DE50306588T patent/DE50306588D1/de not_active Expired - Fee Related
- 2003-07-02 JP JP2004518667A patent/JP2005538974A/ja active Pending
- 2003-07-02 CN CN03815742XA patent/CN1665503A/zh active Pending
- 2003-07-02 CA CA002489396A patent/CA2489396A1/fr not_active Abandoned
-
2004
- 2004-12-02 IL IL16567704A patent/IL165677A0/xx unknown
-
2005
- 2005-01-25 NO NO20050386A patent/NO20050386L/no not_active Application Discontinuation
- 2005-08-10 HK HK05106891A patent/HK1074579A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL165677A0 (en) | 2006-01-15 |
| NO20050386L (no) | 2005-01-25 |
| PL374612A1 (en) | 2005-10-31 |
| EP1519726B1 (fr) | 2007-02-21 |
| JP2005538974A (ja) | 2005-12-22 |
| WO2004004729A1 (fr) | 2004-01-15 |
| AU2003246356A1 (en) | 2004-01-23 |
| DK1519726T3 (da) | 2007-06-04 |
| RU2004139041A (ru) | 2005-07-20 |
| EP1519726A1 (fr) | 2005-04-06 |
| CA2489396A1 (fr) | 2004-01-15 |
| ES2280799T3 (es) | 2007-09-16 |
| CN1665503A (zh) | 2005-09-07 |
| RU2320656C2 (ru) | 2008-03-27 |
| HK1074579A1 (en) | 2005-11-18 |
| ATE354367T1 (de) | 2007-03-15 |
| MXPA05000033A (es) | 2005-04-08 |
| KR20050075281A (ko) | 2005-07-20 |
| US20050197343A1 (en) | 2005-09-08 |
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